


Lonely is the Night

by 1stAmndmntGirl



Series: Team Free Will 2.0 Domestic Ficlets [4]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Attempted Seduction, Awkward Castiel, Awkward Conversations, Awkward Sexual Situations, Blow Jobs, Bottom Castiel, Drunk Dean, M/M, Masturbation, Nipple Licking, Rough Sex, Sex, Smut, Supernatural - Freeform, Team Free Will 2.0, Top Dean, and it’s filthy and wonderful, but seriously, but what’s a plot without porn?, iliary asks the real questions, just so much awkward, porn kinda with plot, there’s sex in this
Language: English
Status: Completed
Published: 2014-02-01
Updated: 2014-02-01
Packaged: 2018-01-10 18:49:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,173
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1163232
Author URL: https://archiveofourown.org/users/1stAmndmntGirl/pseuds/1stAmndmntGirl
Summary: <blockquote class="userstuff">
              <p>Dean Winchester can’t stop thinking about that fateful night before the angels fell (read "The Ecstasy of Gold").<br/>He decides to take care of a personal issue, and finds his favorite invader of personal space.</p>
            </blockquote>





	Lonely is the Night

Dean couldn’t sleep. He’d tossed and turned for hours, and the half bottle of Jim hadn’t helped. He had gone to sleep relatively early (for him), and apparently, the ceiling of his room was just too interesting to look away from. He’d traced every pattern on the damn thing four times over, and still he couldn’t keep his eyes closed. Closing his eyes got him in trouble lately.

Sighing heavily, he pulled the pillow on the bed beside him over his face, trying to block out his own thoughts. They were apparently as stubborn as he was, because they wouldn’t fade, no matter how much he begged and pleaded himself. In fact, they only became more vivid, and he felt his flesh aching. Burning.

This was so stupid. He shouldn’t be affected like this by anything, let alone his best fucking friend. And it wasn’t like Cas had even done anything overtly sexual (other than that whole fucking-him-in-the-ass thing months ago). In fact, the whole thing with him sleeping with that reaper proves well enough that he had a thing for women. He was straight, just like Dean.

He snorted. Yeah, straight. Right. As of this moment, Dean had been straight for thirty-three of his thirty-four years, except that one night when he was seventeen. And the other time when he was twenty-three. And the time when he was twenty-seven.

Well, Dean had been mostly straight for thirty-three years. This past year, that flew out the window as he came to terms with how things really were for him. Did he like chicks? Hell yeah. They were soft, curvy, and when he made them come, their high voices screamed his name in a way he loved. Their nails were long and sharp, and they marked his flesh when the sex was good, and they raked bloody rivets down his back, shoulders, arms, and chest when the sex was great.

But, on the other hand, guys were fantastic. They had power, a rougher touch (usually), and he knew that when their voices broke as he pushed them (or drew them) over the edge, that it was real. Calloused hands clinging to his back as he pumped into them hard and fast, desperate to both make it last and end it soon, as it was all so much, and so perfect. He could plant his hand on their hard, muscular backs as he took them from behind, forcing them to howl out gibberish when he hit their spot.

Dean bit back a groan as his eyes opened back up and stared at the ceiling. He needed release more than he could bear, as he hadn’t had a good ride since the night before the angels fell so many months ago. He’d been living in the bunker with his brother, a kid he considered his son/kid brother, a fallen angel, an ornery kinda-demon, and two hairy mutts who peed on anything and everything he loved.

As much as he wanted a repeat of the night Blondie drugged him and he had Cas fuck him into oblivion, neither man had mentioned the incident since it happened. Dean had been mortified by his actions, his unyielding want to touch and be touched by his best friend, and couldn’t bring himself to talk about it. And Cas must’ve known something was up, because he had never approached the subject.

It was still between them, as no one else in the bunker was aware that it had even transpired, and that was how Dean wanted to keep it. His sex life with women was one thing. Actually, it was many, many things, but that was different. That was normal. That was how he was supposed to be. He wasn’t supposed to get hard at the thought of fucking his best friend.

He turned over so his face was buried in his pillow, and he growled in annoyance. It was too late in the night to go out and pick up a barfly for a quickie, and there was no way in hell he would approach Cas about his physical wants and needs. Not yet. Not happening.  
He shifted, and his lead pipe of a cock rubbed against his boxer briefs in anguish.

“Fuck,” he swore. It was down to two options: take a cold shower and convert Led Zeppelin lyrics into Latin—again—or get quick with some solo action. Since the lyrics on Physical Graffiti could only be translated so many times before it became a mindless chore, he voted for the latter, and his dick agreed.

Remaining on his stomach, Dean scooted his knees up a bit, and gave his hand a bit of room to find his slightly smaller self and take hold. His grip was tight, and his hand cold enough to make him gasp into his pillow, his bottom lip catching on the fabric as he began to stroke.  
His eyes were closed, and he remembered the night he spent with Cas. The desperation. The fever. The absolute certainty that he would die if Cas hadn’t touched him.

Moaning softly into the fabric of his pillow, Dean twisted his wrist so his stroke veered right. His hand was still cold, but warming quickly, and his calloused palms added a rough texture to the act.

He thought about the texture of those satin panties against his dick, and Castiel’s mouth, hot and wet, sucking at him. That tongue lapping at him so innocently, yet so sinfully. Those bright blue eyes staring up at him as he rocked and reeled from the touch.

“Oh, oh fuck!” he cursed, louder than intended.

Biting the inside of his cheek, Dean ground down against the mattress, his cock grinding against the jersey cotton sheets. It wasn’t enough, not nearly.

Bringing himself back up, he twisted his wrist and scraped his thumbnail against the ridge of his head. It was one of his best moves, and while it was good, it wasn’t cutting it. He needed more.

Was he too drunk?

Fucking whiskey, he swore internally. If tonight was the night he suffered from the ill-timed case of whiskey dick, he was going to punch someone in the face. Probably himself, but still. He was going out of his mind, and he just couldn’t come.

He thought of straddling Cas, feeling full and swollen. The veins in Castiel’s neck when he tilted his head back. The fucking holy tax accountant popping his hips up into Dean in perfect rhythm while the hunter lost all sense of control.

Dean used his free hand to push himself up, so that he rested only on his knees with his eyes to the wall. He couldn’t focus his vision, but he mentally pictured a projector throwing up images on the wall of his best friend fucking him in the ass. Fucking owning his ass.

“C-Cas,” he moaned as he fucked his hand.

“Hello, Dean.” He heard from right next to him.

The hunter looked over to see his wettest dream and worst nightmare standing beside his bed wearing nothing but a pair of borrowed pajama bottoms. His hair was disheveled, and he hadn’t shaved in probably a week.

God, was he pressing every button he could.

Realizing how compromising his position truly was, Dean didn’t know what to do. He had been caught by fathers, mothers, daughters, and more than once, a husband or boyfriend (although he wasn’t about the taken ones), and in those situations, he had always been able to react somewhat appropriately. A smirk before running out the door was usually the case, but sometimes, a “Hey, how’s it going?” sufficed. And in one instance, an invite for a threesome that went very well. But to have the object of his confusion standing right next to him, watching him jack off and moan his name? Yeah, Freud probably wrote something about that.

So, not knowing what to do at this point, Dean sighed drunkenly and looked at his best friend. “Hey Cas, what’s up?”

“The bloodflow to your penis?”

A joke. Cas casually walked in on Dean jacking off, and he made a sex joke. What the hell had the world come to since the angels fell?

Blushing, and allowing some of that blood to flow to his other head, Dean cracked an awkward grin and chuckled. “That was a good one, Cas.”

A small smile graced the former angel’s mouth, and then it faded as Castiel looked him over.

“Is there something I can help you with, man?” Dean asked as he tried not to see the tenting in his friend’s pajama pants.

“You said my name just now. Are you thinking of me?"

Oh, fuck. Dean’s dick gave an unwanted throb, demanding for attention.

Letting go of himself, Dean ran his hands through his hair and wondered how life ever got this crazy. He counted to five before bothering to reply.

“Cas, uh, yeah, I was.”

Castiel stood still, watching Dean’s movements. His sharp eyes observed the high blush in Dean’s cheeks, the slight wilt to his cock, the nervous hands and eyes that skittered over the room. He contemplated quietly for a moment.

“Sexually?”

Dean collapsed face-first on the bed, not caring that his bare ass was in the air as he tried to hide his cherry-red cheeks.

Cas took a step closer, and put a hand on Dean’s shoulder before asking, “Dean, are you okay?”

“Kill me. Kill me, then salt and burn my bones,” Dean grumbled into the pillow dramatically.

Unsure of how to proceed, Cas patted Dean on the back, as he’d seen the brothers do to one another. “There, there.”

A shudder ran through the hunter, and forcing himself up, Dean rolled over, covered himself with the blanket, and leaned back on his elbows, his face towards the ceiling.

“Yeah, Cas. It was sexual. I was jacking off and thinking of you, but more specifically, that night at Blondie’s. Okay? Now, please kill me.”

Castiel thought a moment, then leaned over and planted his lips on the hunter’s, startling Dean into pushing the former angel away.

Taking a step back, confused, Castiel looked at his friend before inquiring, “Why did you push me away?”

Dean sat up, rigid in more way than one. His eyes were wide as he looked the angel over. “What are you doing here, Cas?”

Brows furrowed, the other man stated the obvious, “I am trying to seduce you, Dean.”

One part of Dean was elated, another confused, and the last guilty, but the guilt wasn’t as strong as the others yet. “Should I ask why?”

Annoyed at this point, Castiel got on the bed and straddled Dean, one leg on either side of his slender hips. He leaned down and kissed Dean again, irritated when he didn’t get the response he wanted because his partner was wigging out.

“Dean, I have been waiting for your go-ahead since the night before—the night before I became human. I have wanted you since then, and I know you want me, too. So, I am trying to seduce you, like the book said.”

Rock hard and barely able to refrain from grinding against the other man, Dean asked through clenched teeth, “What book?”

“ _How to Seduce Your Man_.”

Dean really didn’t know what he expected.

“Where did you find this book?”

Sighing heavily, Castiel replied, “I found it in a bookstore in town. And before you ask, no, Crowley, Kevin, and Sam do not know I have it, nor do they know my intentions.”

Breathing a sigh of relief, Dean nodded.

Castiel sat back, his rear resting on Dean’s erection.

“So, are you seduced?”

Carding a hand through his hair, Dean crossed his eyes and asked Cas, “Man, are you sure you want to do this? This is about thirty-seven forms of wrong, immoral, and dirty.”

An eyebrow rose. “Dean, I am well aware of the moral ramifications of sodomy. That said, most of that humans put on yourselves.”

“I mean, Cas, that I’m a pretty fucked up guy. Are you sure you want to get your hands dirty with me?”

Looking displeased, Castiel stared down at Dean, and with a clipped tone, he stated, “Dean, I am well aware of you are and what you have done, as you are aware of my history. I think we are past that. Now, are you seduced, or not?”

A relieved smirk snaking across his face, Dean grabbed Castiel by the ass and said, “Call me seduced.”

“Okay, Seduced.”

Dean hungrily took Castiel’s mouth with his own, his tongue tracing the other man’s lips before he sought entrance. Castiel went along with it, content to follow the experienced hunter’s lead as he thrust his pelvis down, eliciting a groan from his lover.

Their mouths mashing messily for a moment, Dean reveled in Castiel’s hands on his chest, anchoring himself on Dean’s nipples like he was unsure of what to do.

Dean’s hands were gripping Castiel like he didn’t know how to handle this. He wound his fingers in his hair, he clutched his biceps for dear life, he groped and squeezed Castiel’s tight ass, and he lightly grazed the inside of the man’s thighs. He couldn’t stop touching him, just like the night at Blondie’s.

He was so hard he hurt, and he wouldn’t be able to deny himself much longer. Apparently the whiskey wasn’t the problem, it was the lack of help. And this was far from fair to Castiel, but if filthy sex was going to be a regular thing, then he could make it up tenfold another time.  
“Cas,” he growled, his voice cutting through the other man’s quiet moans.

Pulling back, Castiel looked at him, his expression flushed, his eyes glassy.

Trying to clear his throat (and his head), Dean said, “Man, I can’t hold out very much longer. I’m gonna lose it if we don’t hurry this up.”

Nodding absently, Castiel went back to kissing him, but Dean spoke into his mouth, “How do you want to do this? Last time, there wasn’t much of a choice. Do you want to finish with our hands? Do you want me to blow you? What do you want?”

Cas looked puzzled, and then it dawned on him. “I need you to fuck me,” he responded, his voice like gravel.

Dean didn’t know what to say. Time and time again, Cas never failed to surprise him or catch him off guard, and repeating his exact words from their one night together? Yeah, he hadn’t expected that.

“Dean? Did you hear me?”

Dazed, but bobbing his head in agreement, Dean replied, “Yeah buddy, I heard you. Are you sure?”

A look from Cas was all he needed to be assured.

“Okay, uh, this is going to be pretty uncomfortable. Let me up so I can grab some lube.”

Cas rolled off him, and Dean shot up, hyperaware of the tire iron slapping against his thigh, and of his audience’s eyes on his form.

He fumbled around in drawer of the highboy, and realized the lube was gone. Again.

“Goddamnit, do I have to lock my door to keep that fuckin’ prophet outta my stuff?” he snarled.

An awkward throat clearing behind him turned his head.

“You?”

Castiel shrugged, looking preposterously human in doing so. “I needed it, and I didn’t have any money.”

The image of Castiel touching himself, groaning and writhing on the bed set Dean’s nerves on fire. “Okay, is it in your room?”

“No, I brought it with me in case my plan worked.”

Thanking both Heaven and Hell, Dean walked back over and held his hand out. “Give it to me.”

Castiel stretched out, and then reached into his pajama pocket, pulling out the small bottle. Dean took it from him with shaking hands. It was hard to believe he was more nervous than Cas, but the former angel lay on the bed casually as he watched Dean.

Coming closer, he started to pull off Cas’ pajama pants, which hooked around his stubborn erection, then slid down his muscular thighs. If Dean hadn’t known any better, he would have mistaken the holy tax accountant for a nude model.

“Spread your legs for me, Cas.”

Doing as instructed, Castiel propped himself up on his elbows to watch while Dean basically coated his hand in lube. He looked at Cas, and when the latter nodded, Dean pushed a finger in.

Eyebrows furrowing, Castiel wiggled at the discomfort. “It looked much more fun when you did this to yourself, Dean.”

“That’s because when I did this, I was hopped up on who knows what with the intent to get laid as fast as I could. I didn’t really give a fuck, to be honest,” he chuckled.

Easing the slick finger in and out of Cas, Dean more than coated the tight walls. He leaned down and brought his mouth over the tip of the former angel’s length, sucking hard.

Gasping like a man on the edge of suffocation, Castiel’s back arched and his hands wound tight into Dean’s hair, pushing him down.

Dean allowed to be manipulated as he maneuvered his finger in and out, and then added another. His tongue traced the veins on Cas’ length, and his teeth grazed the underside lightly.

It wasn’t the best blowjob he’d ever given, but it was apparently the best that Castiel had ever received. He gasped and panted and groaned like a cheap whore. His body bucked and wriggled and shook as Dean tore him apart with a hand and two fingers. Make that three fingers, now.

“D-D-Dean,” Castiel whined, high and unfamiliar.

He backed off, sucking lightly and lazily licking the underside of the head. His free hand gently caressed Castiel’s inner thigh to the point of tickling. When he drew a breathy giggle, he used his thumb to press hard into the spot beside Castiel’s length, urging out a moan.

His mouth sore and his project dripping with saliva, Dean carried on, making sure Castiel was prepped well enough for not only his length, but his girth.

Castiel thrust up into Dean’s mouth hard, hitting his gag reflex a time or two until Dean held him down. With a firm hand to the pelvis, Cas tried to wiggle and writhe, but he had no room. He couldn’t thrust up anymore, and instead, his hands knotted in Dean’s hair, and the bedspread. If there weren’t holes in the morning from those desperate fingers, Dean would be surprised.

Speaking of fingers, Dean’s scissored and spread and felt around for the spot Dean knew would make Cas lose it even more. When he found it, he winced at the howl Cas gave, realizing he would probably have to gag the man.

Pulling his mouth away, Dean’s smirk was too proud to hide. He knew what he could do, and he knew how close Castiel was now. The fact that he had almost pushed his friend over the edge just with his mouth and a few fingertips was somewhat of an ego boost.

“How you feelin’ Cas?” Dean inquired, laughter in his eyes.

Cas brought his head up, his eyes dark with lust. “Now, Dean. Now!”

“As you wish.”

He pulled his fingers out and gave himself a few strokes to perk up before he wiped them on the bedspread. Getting to his knees, Dean lined himself up with Cas.

“This is gonna burn a bit. I’m gonna go slow, okay?”

His lover gave a weak nod, his sweaty hair plastered to his forehead.

Taking a deep breath to steady himself, Dean started pushing in, a low groan escaping his lips. It was perfect. Too perfect, really. He wasn’t able to handle this. He didn’t have the stamina to handle this. No one had the stamina to handle this.

“Fuck, Cas. You’re so fucking tight!” he hissed, his eyes crossed.

Castiel probably didn’t hear him, because his back was bowed again and his lips were opened in a silent whimper.

Stopping himself, Dean had to pull himself together. He had to stay in control. He forced himself to close his eyes and consider what boring crap Crowley, Kevin and Sam were doing in the morning. They were going to the farmer’s market for some fresh produce, then the feed store for those two little monsters, and then the library for some fresh information for a case.

Entirely boring, perhaps, but not boring enough to distract himself from the most perfect ass in existence. Or the fact that the ass was writhing.

“Dean, please,” Cas begged, bringing him out of his head.

Opening his eyes and looking down, he saw his best friend staring up at him, his eyes showing his agony.

Panicking, Dean started to pull out. He didn’t have to get off bad enough to hurt Cas in the process.

Before he could get all the way free, though, Castiel’s legs frantically wrapped around his waist. “No,” the former angel panted, “I need more. Please.”

A relieved smile came over Dean’s lips. “Oh thank God. I thought I was going to have to finish in the bathroom.”

He pushed back in slowly, one hand working Castiel’s dick while he adjusted. Slow, easy strokes at a mild pace. A thumbnail graze of the head every so often. A tight squeeze when it wasn’t expected.

Castiel was a panting, shaking mess, his eyes wide as Dean bottomed out, and then paused.

“Tell me when you’re ready, Cas. I don’t want to hurt you.”

Bringing his head up, blue eyes met green. “Now, Dean.”

Taking his word, Dean started moving in and out slowly, his pace easy.

The heat was searing, and the constriction was suffocating. To be able to ride this every day was a dream Dean held onto tightly, hoping Cas felt the same once the high was over.

“Faster,” the man below him moaned.

Dean picked up the pace, thrusting harder and faster as he lost any sense of a logical rhythm. He brought Castiel’s legs onto his shoulders, and leaned down so that he could put his lips on the former angel’s.

Castiel gripped him hard by his hair and the back of his neck, and Dean allowed him. They both moaned and panted when something went right, and they let out small whimpers when something went _very_ right.

Dean shifted his position so that one knee was more forward than the other, and almost under Castiel’s ass. When he thrust in, this position allowed him to graze Castiel’s spot, earning a loud, ragged moan.

He smirked at his friend, enjoying how lost he was in his own pleasure.

As fun as this was, Dean’s legs were cramping, and he was in the wonderful hell that is being too fucking hard. He needed release, and he needed it now.

“How close are you, Cas?” he panted.

With a voice that sounded like gravel in a blender, Castiel replied, “I’m about to fall off.”

Dean thrust in even harder, earning pained cries as he grasped Castiel’s dick and twisted it lightly. When he did it again, Castiel’s body shook as he reached for the coming high.

Swiveling his hip, Dean brushed against Castiel’s spot again and again. Tears of frustration welled in the man’s eyes as Dean pushed him harder and farther than he could sanely go.

“Dean,” he pleaded, “help me.”

Pushed beyond his limit, Dean nodded feebly and stopped thrusting, much to his lover’s annoyance. He brought one hand down to where his hips met Castiel’s, and he gently slid a finger alongside his length. Picking his pace back up, he curled the tip of his finger up, and he got the reward he sought.

Castiel broke hard, a chest-racking sob of relief his only utterance as Dean rode him into oblivion. His back arched, and his hands grasped at Dean’s shoulders desperately. He came hard all over his chest and Dean’s, the sweet sticky mess cool against their hot skin.

Dean followed close behind him, his shout muffled by his falling to Castiel’s chest and biting down on his soft, sweaty flesh. He emptied himself into his friend as his hips pistoned in and out until he could hear something other than the dull roar in his ears.

He pulled his finger out slowly, not even bothering to pull out yet while they were still so sensitive.

Ten minutes or so later, Castiel’s dark blue eyes peered up at him, glassy and unfocused. “As much as I want to do that again, I think I need to wait a bit,” he announced.

“I’ll get us some Viagra,” Dean informed.

“Huh?”

“Pills to take so we can fuck over and over and over without having to wait,” the hunter explained.

Eyes narrowing, Cas replied, “Why don’t you have those already?”

“Kevin took them all, I think.”

“If I still had my powers, I would smite him where he lies.”

Dean could only laugh at how his night took such an unexpected turn.


End file.
